


The Milk of Human Kindess: Derek Cries Over Spilt Milk

by Always_Bottom_Derek



Series: Milk of Human Kindness Verse [2]
Category: Teen Wolf (TV)
Genre: Blue Balls, Bondage, Bottom Derek Hale, Cock & Ball Torture, Cock Piercing, Collars, Dehumanization, Fisting, Human Cow or Werewolf Cow in this Case., Leashes, M/M, Master/Pet, Medical Kink, Medical Procedures, Mentions of Breeding, Mentions of Lactation, Nipple Piercings, Non-Consensual Body Modification, Prostate Massage, Prostate Milking, mentions of mpreg, verbal feminization
Language: English
Status: Completed
Published: 2018-02-02
Updated: 2018-02-02
Packaged: 2019-03-12 11:54:28
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 1
Words: 7,087
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13546800
Author URL: https://archiveofourown.org/users/Always_Bottom_Derek/pseuds/Always_Bottom_Derek
Summary: Stiles bought a Hale dairy-were at auction from Argents' commercial milking operation. But his new milk maker is having a problem producing so he goes to Deaton for assistance.Deaton is happy to help, seeing as he's developed a fondness for Stiles's new stock. Maybe even enough to desire Derek for his own. But the vet's busy schedule isn't conducive to ownership and, as the old saying goes, why buy the were-cow when he can get the milk for free?





	The Milk of Human Kindess: Derek Cries Over Spilt Milk

**Author's Note:**

> Here's another filthy installment for you kinksters....

The receptionist had gone home and it was two hours before the night staff’s shift started. Taking advantage of this window of quiet, Deaton was just finishing up the last of his file updates when the buzzer to the back of his clinic sounded.

Too responsible to ignore it, a tired sigh escaped him as he pushed up from his desk. He shuffled towards the supernatural section of his clinic, his visions of _Masterpiece Theater_ and the bottle of good brandy waiting for him at home growing more translucent with every step.

Seeing who waited outside the glass doors illuminated by the parking lot’s floodlights, Deaton sighed again. Unlocking the door he pushed it open and stepped aside before he got swept up in another Stilinski whirlwind. 

True to form, Stiles stumbled in limbs flailing. The words he’d been mouthing outside followed him.

“Oh thank god, Deaton. I was worried I missed you. Really appreciate you opening the door. I would have tried to wait until morning, but I just couldn’t.

"He’s not right, Doc. I mean, I think we’re reaching critical mass here. He was whimpering… Not like a good whimper… But a bad one… And since I got him, you know how quiet he is”

“Perhaps that’s because you create enough noise for both of you.” Deaton didn’t wait to see how his humorous but valid observation landed. Instead, he peered outside at the dairy-were hanging reluctantly back at the threshold.

He was pleased to see this time Stiles remembered and the leash he held remained loose, not tugging on the wolf’s collared neck. Deaton bent and unlatched the hinged mountain ash moulding at the door’s base, pulling it up so Derek could come in.

“It’s okay now, sweetie,” he urged. Seeing the werewolf was still hesitant he offered a tight lipped smile to minimize his teeth and encouraged, “I know you’re not fond of me, Derek, but Stiles is clearly worried about you. Come on.”

When Derek stepped into the waiting room, his nose immediately twitched and he sneezed. Not like he was sick though. No, it was no doubt a reaction to the scent of the cleaning agents Scott used to wiped the room down with at the end of each day.

Deaton’s dark eyes roved over the dairy-were’s body, a precursory examination of sorts. The Hale milk stud was a fine specimen and outside a little flush on his cheeks and a few extra lines on his broad brow, nothing struck him as particularly noteworthy.

It was a fairly complete visual sweep too, since Derek was bare outside the modesty tack standard for dairy-weres. The short, black-mesh skirt-ish/panty combo supported the wolf’s heavy sack and thick udder and kept the sight of such cumbersome appendages from offending the eyes of delicate onlookers.

Deaton motioned to the wrist cuffs latched behind Derek’s back. “Are those really necessary?”

It seemed a little overboard as far as restraints went, although the way they held his arms behind him and pushed the wolf’s broad chest forward certainly made it easier to scan Derek’s front.

Even as he questioned Stiles’s choice of extra tack, Deaton was pleased to note the heavy rings he’d put in when the wolf had been brought in for his free first vet check two weeks ago had healed wonderfully. They were clearly doing their work too, the tips of Derek’s dusky nipples were already longer and more than twice the thickness they’d been at his previous visit.

Though normally he would have waited until they were in an examination room, since it was after hours and the clinic was empty, Deaton reached out and hooked a finger through one of the rings. He pulled the sliver loop towards him and twisted it.

Dropping his eyes, he enjoyed the twitches that rippled the straining soaked mesh that covered Derek’s groin in response and the sound of his light whimpers. 

“Has he been aggressive to you?”

“Oh, no! Not at all.” Stiles sounded offended at the thought. “He’s a fucking pussycat.”

Derek too flashed Deaton a wounded look too before dropping his eyes again. And to prove his master’s words he did his best to stay still while the vet tortured his nipple.

“He’s such a good wolf. Aren’t you, Derek?” A shiver quaked the werewolf’s solid frame at the praise and Derek leaned in eagerly as Stiles grabbed the back of his head and pulled him in to press a chaste kiss to his forehead.

Stiles laughed when he pulled away and the wolf tried to chase his touch while still holding his position.

“I keep him in the garage at home, mostly. Dad helped me set it up. But he needs a lot of exercise. And any time I take him out unrestrained, it freaks people out. No one seems to understand that he’s nowhere near as vicious as he looks.”

Moving around behind Derek, Stiles unlatched the cuffs and gave a light rub to the dairy-were’s shoulders in apology for the bindings.

Then his hands shifted downwards and he lifted the mesh flap barely covering the milker’s prosperous ass. The combo’s front pouch narrowed to a thin strip at the taint and continued like that up the back; the resultant thong had been swallowed between Derek’s fuzzy cheeks. Stiles rubbed a hand over the supple flesh of one of these.

“It’s a shame really. How quick people are to judge,” Deaton agreed, watching Derek press eagerly back into his master’s hand. His eyes moved from Derek’s hairy butt to his furry chest. Dropping the nipple ring he scratched through the dark swirls over plump pecs.

“Good to see his hair is coming in well.”

Under all the attention he was getting Derek began to make a low, rumbling purr. “Depending on what depilatory those big commercial dairies like Argents use sometimes it never comes back.”

Leaving off Derek’s chest, Deaton stepped back. Derek continued his pleased rumbling until Stiles stopped too. Then the look of sad longing on the werewolf’s face was so comical Stiles chuckled and returned to kneading his milker’s lush rump. The second he did this, one could almost see the stars dancing in Derek’s eyes as he gazed over his shoulder at his owner.

It pleased Deaton to see how bonded Derek had already become to his master: milkers who liked their handlers always provided bigger harvests.

Not to mention, though his quick healing hide had shown no scars, it was clear upon that first visit the wolf had been badly abused during his time at Argents' dairy. It was a testament to Derek’s temperament he’d settled in with Stiles so quickly. Plenty of weres would have gone feral for less.

“Well, it’s good you saw his true nature. And lucky for you, he only looks so fierce, otherwise, I doubt you could have ever afforded a stud of his caliber and breeding.”

Picking up the lead Stiles had dropped Deaton tugged it lightly, encouraging Derek to follow him. Derek hesitated until Stiles pulled his hands away. As soon as he was bereft his master’s touch this time the stud became immediately compliant. Though obedient, however, his body language was stiff until Stiles followed them, filling the quiet hall with chatter.

“Yeah, you got that right. I mean, I know the day Scott and Allison dragged me to her family’s bi-annual stock ‘fire sale’ I was like, ‘what the hell? Why?’ But then when I saw this big lug… I dunno… Something just kind of hit me.”

“That’s not an uncommon experience.” Deaton offered as he ushered them into examining room two, which was specially fitted for treating werewolves. “When people acquire a domesticated supernatural it’s often because they feel some sort of connection.”

“Nah, it wasn’t that. I mostly just felt sorry for him. He looked pretty pathetic." Stiles never discussed the true details of how he'd found Derek, having no desire to revisit the memories of their first encounter. Seeing the hurt telegraphed in the rise and dip of Derek’s bushy brows Stiles reached up and ruffled his dark head.

“I mean, don’t get me wrong. I’m, like, super attached to him now.”

Deaton found it amusing that Derek somehow managed to hold his scowl and simultaneously look pleased at the same time. At least until Stiles’s next words.

“But about the cost thing. I mean,  I got him super-cheap even though I spent my first semester's college savings on him. But now I’ve had him for a bit, things aren't going like I'd hoped.”

Derek shifted uncomfortably looking down. Deaton watched the wolf’s ears turn progressively redder while he waited for Stiles to continue.

“I know when I first brought him, you said he wasn't really 'dick-broke'. And that with all the shifts and things it might take some time for him to get adjusted and really start producing. But it’s been two weeks now, Deaton, and he’s not releasing anything. I mean, he drips whey like cheap faucet, but that’s it. Just … dribbles.

“Since he’s Hale lines I’d planned to make back what I spent on him and put away some more, marketing his milk as private, organic. _Hale and Hearty, Wonder Were-Milk! Use Hale to cure your ails!”_ Stiles said with a proud flourish, clearly tickled by his own cleverness. Then his expression shifted back.

“I can’t do that if I’m pumping a dry well, so to speak… And now this...” He gestured to Derek’s covered but extremely prominent bulge.

The news of Derek’s dry spell had Deaton frowning since he’d run the wolf’s milk sample himself that first visit. He reached over and plucked at the fasteners on the sides of Derek’s loincloth.

“Hmmm. Well, let’s see what we have here.”

As soon as the fabric fluttered down and Derek was left unsupported, the milk stud gave a low uncomfortable whine. Deaton’s eyes grew wide at the sight that met him. 

“Oh my…”

Derek’s hard cock had immediately popped up as much as the heavy ring weighting its head would allowed. The milker’s udder looked perfectly healthy, if a bit chapped. Its shaft was thick, full with blood, and sported a pleasing curve to it despite the strain of the ring. The cherry tip of Derek’s cockhead was shiny, drooling fluid heavily onto the exam room’s commercial tiles. But his milk bag….

Deaton “tsked.” The werewolf’s balls were so swollen with unreleased milk, the weight of them pulled the skin of his scrotum taut. They were dark, almost bruised-looking, they were so full.

“Stiles, how long has it been since you milked him?!”

“You gotta believe me, Doc,” Stiles's voice was hot in response to his accusatory tone, “I gave him a three day break, like you said, but since then, I have been milking him at least every six hours. He’s hard most of the time, like he’s ready… But…

“I tried the milking machine… And when that didn’t work and I couldn’t stand listening to him bawl anymore; I did some research and got a fake bitch sleeve; like the cruelty free dairy sites suggested. When that didn’t do anything, I had Scott bring his Cora by. 

“We induced a heat in her… For Nothing!

“I mean, it did something, but not what I hoped. I think that’s actually the only time his udder's went fully soft since you fixed it. Poor Cora, all worked up. You should have seen her! She ended up riding a wall mounted dildo for three hours until the inducer was out of her system.”

A flush filled Stiles mole-dotted cheeks at the memory. “And after all that, I even broke down and used my hands on him… Which… uh… _Gross!_ Not to mention Lydia found out and has been ribbing me for days about it… But I still did it, ‘cause Derek seemed to be getting so uncomfortable.”

As he defended himself, painting a picture of a dedicated owner, Stiles’s body became animated. By this point he had worked himself up pretty good, his wiry arms gesticulating wildly.

“Pumped him until my arm felt like it was going to fall off… I just kept hoping if I kept it up, eventually the dam would break. You know?!”

“Easy Stiles…” Deaton soothed in the same tone he used on his animal clients, adding, “You’re frightening, him.”

Stiles settled somewhat when he realized this was true: his rescued dairy-were had shrunk in on himself considerably. Derek was silently crying. His cheeks were as wet with tears as the tip of his recalcitrant udder.

“Aw shit…” Stiles huffed and stuffed his flyaway hands into his pockets. “I keep forgetting how much he seems to understand. And just how sensitive this big guy is.”

It was clear to Deaton that Derek was deeply ashamed of his failure, and probably more than a little concerned he was going to get sold off again as a result.

“Well, let me take a look here. There’s no need to cry over spilt milk.” He patted one of the wolf’s plump pecs soothingly. “Or un-spilt, as the case may be.” Deaton chuckled wryly at his own cleverness as he shifted his hand down to examine Derek’s near-splitting sac.

The pressure must have been hurting terribly as the dairy-were uttered a cry and shied away before a finger was even laid on him. Deaton caught Derek’s loose lead up again and started cooing softly at the upset milker.

“Easy now…” 

Once his leash was collected Derek settled right down, though the poor wolf trembled violently. His muscular legs seemed almost wobby when Deaton ushered him up onto the exam table. Given Derek’s history he hated to do this, but he couldn’t risk the wolf injuring himself during the exam, which, considering the state of his balls, was clearly going to hurt.

“Can you give me a hand, Stiles? I don’t want him to bolt unexpectedly.”

Stiles stepped up immediately to assist, attaching Derek’s wrist cuffs to the handy chains welded to the table’s stainless steel sides.  

“I suggest we gag him too. He’s bound to holler a bit. There’s a variety of disposable ball gags in that drawer there. You pick the size you think he can handle. Jaw stretched, but not extreme.”

While Stiles distracted Derek’s front end, trying to get the stud to open his mouth, Deaton, careful not to spook the sensitive were, skillfully grabbed Derek’s fat, thirteen and a half inch hard cock and clipped another restraint chain to its ringed head.

“Ah, that’s better.” He stroked down the sweat slick side of Derek’s muscular flank. “I’ve never yet had a milker try to jump off the table once an udder was secured.”

With Derek positioned on his hands and knees, Deaton made quick work strapping down his calves and securing his ankles. Once the werewolf was immobilized he reached out and gave his swollen testicles a squeeze. Derek bellowed behind the gag when his sac was touched for the first time. His muscles flexed and rippled, straining against the runed restraints.

“Oh, yes…” Deaton hummed, weighing the hot flesh in his hands. “You’re all backed up. Aren’t you, dear.”

Stiles watched from the side, concern written all over his face at the sight of his usually stoic acquisition openly sobbing.

“What’s going on, Doc?”

Stiles pulled some crumpled tissues from his pocket and stepped up to catch the snot dripping from Derek’s nose. “I mean, you tested him, said he had some of the highest quality milk you’d  ever seen. 'Grade A'…

“You didn’t have any trouble getting that sample did you?”

When he said this the vet paused palpating Derek’s baseball sized left gland. Realization dawned on his features.

“No Stiles, I didn’t. In fact, now that you mention it, he seemed a bit swollen then and I had barely penetrated him when he came. Filled up three specimen cups no problem.”

Deaton cocked his head to the side considering something. Then he set a hand on each side of Derek’s ass and pushed the dairy were’s fat cheeks apart. As soon as Derek’s hole was clearly displayed he began nodding his head. 

“Yes… Just as I thought. Come take a look.”

Stiles stepped over and his brow wrinkled seeing the way Derek’s hole fluttered. It was pulsing, the rim pink and puffy, opening and closing like a tiny, gasping mouth.

“What the fuck?”

Deaton reached over and grabbed Derek’s balls ignoring how he howled. He rolled one and then the other. Each squeeze had the milker’s hole yawning wider and wider.

“I’m sorry to say this but Argent’s clearly gave you fake papers. It’s very rare, especially for a male of Derek’s proportions, but what you have here isn’t a stud at all, Stiles. Your dairy-were is a bitch.”

“A bitch? What? Does that mean he can’t come? But you said… Please don’t tell me he’s worthless...”

Seeing the question on Stiles face, Deaton sighed. Every day he had to explain the most simple things to animals’ ignorant owners. He gave an absent pat to one of Derek’s calves: since at the revelation of his “defect” and Stiles’ questions, the poor dairy-were had started brokenly sobbing.

“A bitch can’t come from just the stimulation of his udder, your milker needs to be penetrated to produce.” Deaton 'tsked'. “No wonder they let him go. Most dairies are ridiculuosly prejudiced against male bitches.

"You can get milk from a bitch like Derek though. Good milk,” he assured. “The process is just a little more involved than most are willing to go through.”

“Great!” Stiles huffed, flinging himself down into one of the room’s were-proof chairs. “So tell me. What do I have to do. I need to make my money back on this deal, Deaton! Not to mention… All the alterations my dad made to his garage so I could go into production.”

Deaton took a latex glove from his pocket and pulled it on one of his hands with a snap. “I think the best way for me to instruct you in how to properly milk a bitch is to show you.”

Pulling some lube from a drawer, Deaton generously coated two fingers. The second his latexed digits started tracing Derek’s pucker, the still weeping dairy-were whined and pushed back as much as his bonds would allow. 

“Yes, that’s it, Derek.” Deaton watched as the wolf’s rosy, bitch hole slurped at him the moment he began to press in. It was immediately clear on entry the lube was redundant the way Derek's own slick oozed around his fingers. “You just need another kind of milking don’t you, sweetie.”

If the volume of Derek’s moaning was anything to go by, he was in total agreement. His plump buttcheeks jiggled as he started pulsing his hips, trying to work the fingers deeper into himself without bouncing his balls too much. When he did, his near constant groans would break with a little hiccupping whimper.

“Oh… I can feel his prostate. It’s quite enlarged too.” Deaton murmured as his skillfully began massaging it.

At this point Stiles got up out of the chair, moving in to get a closer look. In addition to the chain, a long string of precome connected Derek’s pierced cock to the table now too. He reached forward and swiped his fingers through the clear fluid.

“Smells sweet.” Stiles sighed… “But that’s not the color we want.”

Deaton frowned, frustrated by the young man’s impatience. “As I said before, he's backed up, Stiles, badly it appears. So this will take a few minutes. Poor thing,” The vet patted Derek’s round rump with one hand while his other pumped. “After all this time, not realizing what he was…”

He shook his head at his own oversight. “If a bitch isn’t regularly expressed it can cause all sorts of lasting problems. I hope it’s not a severe as I fear.”

“Well, shit.” Stiles huffed in annoyance. Eyes fixed on the fingers pumping into his dairy-were, his expression was one of curious revulsion. “And am I gonna have to do that every time? I mean, stick my fingers in his ass?

“It’s his cunt too” Deaton offered, hoping this might render the prospect less objectionable, though his eyes stayed fixed on Derek’s neglected bitch hole. ”But with the latex between you, I don’t see why it should be an issue. If you’re really so averse, however, you may want to invest in a mechanical stimulator.”

“A fucking machine?”

Sighing at this, Stiles moved down the examination table and hooked a finger through one of Derek’s nipple rings and began to bat it back and forth. “How am I ever supposed to get ahead with all these expense?” He watched the way the ring-play made the wolf quiver harder and Derek’s eyes roll back in his head.

Deaton thought the young man and milker were a good match, so it was concerning how defeated Stiles sounded. Not to mention, he’d spent a number of hours since Derek’s first visit dreaming about having a long, fruitful medical relationship with his newest patient.

Knowing that Stiles's ADD rendered him easily frustrated and often impulsive, he hated to think he might get rid of Derek in a fit of pique when the situation was entirely salvageable. Noting the way the were-bitch’s channel suddenly clenched around his fingers, he looked up and saw Stiles teasing Derek’s tit. It gave him an idea.

“You know Stiles, it’s not widely known, but with a little assistance male bitches can make more than one kind of milk.”

Stiles stopped tormenting Derek’s nipple and peered at Deaton over the curve of his dairy-were’s plump ass.

“Really?”

“Mmmm,” Deaton nodded as he added another finger. “You could have three udders working for you eventually, instead of one. With a little effort.”

Derek’s ass was making liquid gasps now as he was finger fucked. His rosy hole dripped with even more slick, which was very promising indeed.

“In fact, with the the right treatment and a little counter-evolutionary magic, I might even be able to incite all his vestigial bitch organs to resume.”

“What does that even mean, Doc?”

“What I am trying to say, Stiles, is that we might be able to turn your bitch into a breeder.” He added while Stiles was processing this new information, “Think about it... With him being Hale stock, his calves would bring a pretty penny.”

Putting a hand on a slick shoulder Stiles gave Derek a few pats. He leaned around so he could see his milker’s strained, tear-stained face. Drool dripped from the wolf’s gagged mouth and hung in strands from his stubbled chin, leaving his front end as sloppy now as his back.

“Would you like that? Derek… A big belly full of calf? Bet these tits of yours would get even bigger once that milk came in. You’d probably look so pretty like that.” Stiles turned back to Deaton.

“Would it be an expensive process? The turning?” He had to raise his voice over the noises Derek was making. Need or protest, it was difficult to tell with the gag.

There was a growing puddle on the table now, Derek leaking bitch juices from two places, but still no milk. Deaton sighed, ignoring Stiles’s question for the moment.

“I think, sadly, this might be a little worse than I thought…”

When he removed his fingers, Derek whined at the loss. The vet’s heart gave a little twist at how much the poor thing was suffering. Quickly he stripped the glove off and stuck his bare fingers in Derek’s ass. At the skin to skin contact the wolf’s cock jumped and spurted a bit of cloudy fluid.

“Well, at least you won’t need to invest in that stimulator now.”

Stiles frowned and tipped his head in question.

“Sometimes this happens with bitches of either gender, especially if they’re over-used.” Deaton shook his head at humans' cruelty in the name of profits. “Not uncommon, for big commercial outfits like the Argent’s.

"It could be, if they were harvesting from him, despite his bitchness, they could have had your poor Derek all but living on a “fucking machine”, as you called it, to get as much milk from him as possible. It's against welfare regulations, but it happens sometimes. Not every dairy is eithical...

“They do that because of the were’s healing powers: a male bitch's hole tightens up so quickly that to have to prep him again at each milking isn’t time efficient,” Deaton explained. “And they can’t use plugs, because a were-bitch’s cunt will seal around that too, making it just as much work to get out as a regular prepping.

“If that was the case, he’s built up what known in milkers as an ‘object-immunity’.”

“So, more likely than not, your Derek needs skin to skin touch to produce now. Yet another reason for Argent’s to discard him.”

Deaton stopped to add more lube, despite the surprising amount of slick Derek’s ass had started making once his body recognized flesh and not latex. He wanted to make sure the poor dairy-were was comfortable for what was coming. Or at least as comfortable as he could be.

Stiles had shifted back down beside him to watch as Deaton coned his four fingers and began to open Derek up. For once, the young man was quiet, eyes raptly watching the hand pumping into his dairy-were’s glistening hole.

Deaton appreciated the silence, especially since he’d worried for a moment that Stiles, with that acute mind he had, might ask how he’d made his stock come so quickly last time if Derek had “object immunity.”

It would be awkward to admit he hadn’t worn a glove.

From the time he’d been a boy on his famliy’s supernatural farm he’d always loved the warm, wet, velvet feel of these creatures’ insides. Ass or pussy, it didn’t matter. So he conducted all his reproductive and milking exams on his magical patients barehanded when an owner wasn’t present.

It was a little private perk of his practice.

Though he imagined most owners wouldn’t have cared, he preferred not to advertise his quirks. So there was something thrilling tonight, having Derek’s master here watching as he pumped his hand down to mid-palm into the Hale milker’s lovely ass.

The slick-wet hair around Derek’s asshole lay flat, doubly dark against pale skin, it framed his hand-filled hole beautifully. On his next withdrawal, Deaton held his thumb down against the flat of his palm.

This time when he pushed back in, the dairy-were’s rim paled as it was stretched to capacity. Feeling the strain, Derek lunged forward in his restraints, He stopped short though when Stiles grabbed the chain attached to his udder.

“Easy, Derek.” Stiles’ voice was gentle but firm. “That’s a good bitch.”

Deaton smiled to himself watching Stiles try out the new term for his milker. The subtle curl of the young man’s lips told him he’d found it pleasing.

“We’re so close… Easy there. Come on now, sweetie. Open up…” Without breaking the rhythm he’d set, Deaton slapped Derek’s ass. The sting of the spank made the wolf clench down so hard on his hand it was almost painful, but when it relaxed after, Derek’s tight bitch hole was noticeably looser.

“Stiles in that drawer are some manual milkers' bags. Will you grab one for me?”

Deaton slapped Derek’s ass again. The werewolf sobbed and shuddered but stayed otherwise still, trying to be good for his master. By the third strike one of Derek’s fuzzy round cheeks sported a growing red glow.

“I recommend the half gallon. This is going to be a big harvest. I only hope with the wait it hasn’t soured.”

Stiles grabbed the milking sleeve with the half gallon baggie attached. Following the directions the vet gave him in between spanks, he unchained Derek’s cock and used the milker’s whey to slick it, since lube would have contaminated the milk.

Careful of the heavy piercing, Stiles slid the sleeve on and gave Derek’s udder a few tugs of encouragement.

 "You’re gonna feel so much better, buddy, once you come. Yes, you are… Come on, Der… be a good bitch for me…”

Deaton thought it was a lovely moment, the sort a vet lives for: the tender interaction taking place now, the connection between owner and owned. Not to mention the beautiful sight of the bright red expanse of fat milker ass spread before him and the silken, liquid feel of Derek’s bitch channel around him.

With Stiles watching, Deaton gave Derek one last smack. It was hard enough to make both the dairy-were’s cheeks bounce, but it worked. With a wet 'slurp' on one end and a pained wail at the other, Derek’s hole finally opened up enough. From where his hand had been caught on his thumb’s last knuckle, with this new bit of stretch Deaton's whole hand popped inside Derek and was swallowed up to the wrist.

Rubbing his free hand lightly over the hot, red skin of Derek’s spanked bottom, he waited a few moment for the bitch to adjust. Once his fist was in, Derek had dropped down all but boneless, his chest pressed to the examination table, head turned to the side facing Stiles.

“There, there. Doesn’t that feel good, sweetie?” Deaton cooed.The leg restraints were clearly the only thing holding the overwhelmed bitch’s back end up, but as far as presentation posture went it was nigh perfect.

“Yes, I bet that feels right. Like a big old knot. That’s what you’ve been needing, isn’t it, dear? You don’t need anyone tugging on your fat udder, you’ve been waiting for a nice, big stud’s cock to fill you.”

Derek gave a broken whimper at the words and new tears rolled down his flushed cheeks; his dark head jerked in a way that could have been read as a shaky nod.

“Good… Good… You’re being so perfect.” Without pulling out, deep inside the bitch’s slick channel Deaton worked it loose until he could close his hand into a fist.

“Why don’t you take his gag off there, Stiles, so he really breathe. I think he’s settled now. Then I’ll have you hold the sleeve tight around his udder while I express him.”

Stiles was quick to comply and didn’t even act too disgusted when Derek’s sloppy mouth caught his fingers as he worked the ball loose. In fact, he even kept them there, allowing the dairy-were to pepper them with grateful kisses.

And it didn’t escape Deaton’s notice when Stiles slipped two fingers fingers into Derek’s mouth, pulsing them over tongue while the milker anxiously suckled them. This was promising. Because if Stiles could tolerate or even come to enjoy Derek’s mouth, the bitch’s other hole shouldn’t be too difficult to get used to. 

“Yeah, you didn’t like that gag did you, Der?”

Stiles fought not to laugh at his wolf’s broken worship. He pulled his hand away and tried to dry his fingers in Derek’s bangs, but with all the fevered sweating he’d been doing dairy-were’s hair was just about as wet as his mouth.

“You gonna give me what I want, Der?” Stiles asked in the same singsong voice as he shifted so one hand was wrapped around Derek’s plastic-wrapped udder, the other rested on the bowed broad back, rubbing soothing circles.

“I wanna keep you, I really do. But you gotta give it up for me, buddy.”

“Oh, your bitch is going to give it up, Stiles. Don’t you worry.”

With that, Deaton began pumping his fist in Derek’s ass. It was glorious, a hot, wet seal around his hand, his wrist. Consciously working himself deeper, he didn’t stop until half his thick, dark forearm had disappeared into the Hale milker’s hole.

As he did this, Stiles was making a conscious effort to keep his eye on Derek’s udder. He gave out a small “Whoop!” When the first real cream began to spurt.

Meanwhile, Derek just laid there on the table. Wanting to please, he’d given up all resistance completely. He stayed limp and pliable as Stiles and Deaton worked him over. No more crying even. He just panted, open-mouthed and ragged, allowing the pleasure/pain of the fisting to wash over him.

“Oh, sweetie, you’re being such a good bitch. Lying there, taking my fist. You might be big but you're just a needy little thing at heart, aren't you?” Deaton all but crooned, entranced by the feel and the sight of the dairy-were’s pretty submission, “Bet you’re imagining a big, hairy, hard-muscled alpha stud on top of you. Filling you with his milk. Feeding your hungry pussy. 

“Knotting you up until you think you’re going to split apart. His knot bigger than the head of the calf he’s going to fuck into you.”

At these words Derek uttered a cry and it was like someone flipped the valve on a hydrant.  Jet after jet of were-cream shot from the milker’s massive udder. Seeing this, Deaton picked up his pace.

Derek made soft, pained huffing noises now as Deaton started pulling his fist out of his ass completely and punching it back in.

The thrusts of this set the heavy nipple rings swaying. Stiles lifted his hand from Derek’s back to his sensitive tips and began alternating pinches to each one in time to squelched rhythm of the vet’s punches.

“That’s right, Derek. Fill that bag up, bitch.”

Stiles squeaked in surprise when he pulled hand away from one of the wolf’s nipples as saw his fingertips dewed with cloudy drops.

“What the?” He waved a hand at Deaton. “What’s this?”

“Excellent.” Deaton was panting himself from the exertion of his fist fucking. “That just means he's apt to be responsive to a 'turning'. And that he’s getting close....”

Making sure the bulb of his thumb was set over Derek’s prostate, he kept his hand inside the wolf’s ass now and pumped viciously. Derek’s head ducked and he tried to sink his teeth in his own shoulder to stifle his screams at the brutal fuck and as the dam burst and he started coming for real.

It was all Stiles could do to keep hold of Derek’s cock. His udder writhed like a loose fire hose as streaming cum rushed into the bag with such rapidity it looked like Derek was pissing milk. Soon the bag was taut and straining. Fluid surrounded Derek’s udder in its sleeve. It welled up and began to leak out from the plastic sheath's opening and down Stiles’ closed fist.

Deaton didn’t even need to move now, the way that Derek’s bound hips bucked. Caught in his orgasm the bitch was doing a fine job of riding his fist on his own. Once the dairy-were stilled, he resumed his pumping. Wrecked and over-stimulated, Derek turned his messy face and pressed his forehead to the cool steel table before he burst into fresh tears.

Deaton smiled sadly, understanding how uncomfortable this must feel now that Derek had come. “Oh, I know, sweetie… This must hurt something terrible, but we’re not done yet.”

While Stiles pulled the milking bag off before it burst, Deaton went to work continuing to fuck Derek until he was sure the milker didn’t have a drop left in him.

“Since you have been holding out, we need all of it, Derek. You need to be completely empty if we’re going to keep you healthy…”

Now that the milker’s sac had shrunk considerably and without Stiles’ hand or the milk bag obscuring his view, Deaton was able to enjoy pathetic twitches of Derek’s still big, but deflated udder as it spat out the last of bits of fluid. Above this, the red ruin of the bitch’s cunt glowed around his wrist still.

With this picture before his eyes and Derek’s soft broken bawling in his ears, while he was usually the pinnacle of professional detachment, Deaton had never been so hard in his life.

It was a great disappointment when he realized he’d finally milked Derek well and truly dry. He pulled his hand out before Stiles could reasonably accuse of him of just “playing” now. The exam room echoed with a wet 'pop!' and the sounds of lube and slick farting out of Derek’s gaping ass as his fist left.

After running his fingers over the dairy-were’s puffed, stretched-open rim Deaton patted Derek’s ass with his sloppy hand. “There, now. That’s all over, dear. Don’t you feel better?”

The only answer he got was the wolf’s shuddering under his palm. Deaton kept his hand there, resting. That fisting had worn him out a bit, truth be told. After a couple minutes of catching his breath he moved to one of the room’s plastic chairs and collapsed into it.

He motioned to Stiles and watched as he set about freeing his stock. Derek slid down off the table into a heap and wrapped his arms around Stiles’s lean legs. Clinging to them, he sniffled.

Stiles looked down at his bitch with something akin to fondness. He ran his fingers through the dairy-were’s wet hair. “It’s okay, Der. You did good, buddy.”

When this only made Derek burrow in further, his sniffles increasing, Stiles sighed, “look, I’m going to keep you, okay?”

From where he sat observing, it was another touching moment to witness: the way Derek’s head lifted, the pure, raw hope on his face. Stiles chuckled. Extricating himself from Derek’s koala grip he squatted down and pressed a fresh kiss to Derek’s shiny forehead.

“Yeah, I guess you’re worth it, even if it is a little extra effort. I’ll work it out. Alright?” Then Stiles stood and surveyed the wreckage of the exam room. The table was puddled with milk and slick and spit. He hooked a thin finger in the D-ring of Derek’s collar and tugged.

“Okay, enough Hallmark here. Let’s get you up so you can help clean up your mess while I talk to the Doc.”

Though clearly exhausted, shaking with gratitude, Derek rose. He climbed back up on the table all on his own, only in the opposite direction he’d originally occupied it and began licking up what he’d spilled.

Grabbing the near bursting bag Stiles carried it over to the vet and held it out.

“I’ve never developed a taste for it raw,” he admitted. “Do you want to give it a go? Tell me what we’re working with here?”

Deaton took the bag, carefully and loosened the sleeve where Stiles had tied it off. It wasn’t protocol but… He sucked the sleeve into his mouth and allowed the wolf’s milk to flood it. After the first swallow he couldn’t help but gasp.

“Hot damn…. It’s amazing.”

“That good, huh?” Stiles smile was wide, but there was something in his eyes that was scheming.

Far from soured, letting it ripen in Derek’s sac had just the opposite effect. It was the best werewolf Deaton had ever tasted and he felt the vitality of the milk invigorating his cells immediately. Unfortunately, this just made the uncomfortable erection he sported even harder.

His arousal had not gone unnoticed. Stiles whistled. Derek’s head popped up from the exam table he’s been so diligently licking.

“That’s good enough for now, Der. Come on over here, bud. Deaton’s got a treat for you for being so good.”

His hands occupied with the milk bag, Deaton was too stunned to move when Stiles reached over, undid his trousers, and pulled out his thick, dark cock. Derek slid off the table and crawled between his spread thighs without hesitation. After a couple introductory sniffs and a licks the bitch swallowed him down.

“So... “ Stiles settled down into the chair bedside Deaton, watching Derek’s dark head bob between his legs.

“Will that bag cover the cost of turning him into a full bitch? A breeder?”

The warmth of Derek’s milk buzzing his body and the feel of hot, wet mouth on his cock had left Deaton momentarily at a loss. He groaned and nodded as Derek did something wonderful and tricky with his tongue.

“Good. Good.” Leaning back in his chair Stiles stretched his arms out. “So, now we know what his problem is… How many times a day should he be milked?”

“T-twice…” Deaton sighed and shuddered as Derek picked up his pace.

“So then, do you make house calls? Cause to be honest, I almost kinda maybe puked a little bit in my mouth when your fist just popped inside Derek’s ass... er  cunt…  whatever you wanna call it. Okay, well not almost kinda… I  maybe definitely puked a bit.”

Stiles reached over and took the milk bag from Deaton’s hands. His voice rose a little as he continued, making sure he could be heard over the sounds of Derek’s choking and slurping.

“I mean, with this 'turning' stuff you’re gonna want to be checking on him regularly anyway. And then there’s the breeding and the babies… That’s a lot of vet care. Sooooo…. I figure we can make a trade?”

As soon as they were free, Deaton’s hands hand dropped and wound themselves in Derek’s damp hair pulling the milker’s mouth onto him completely. The way the wolf’s throat surrounded him, he fought to keep his eyes on Stiles, not rolled back in his head like they wanted to at Derek's sweet suction.

“You help me get back what I spent on him _and_ make a profit…  And I’ll keep you in his milk and whatever other sort of ‘in him’ you might want... Sound reasonable?”

Deaton’s tongue traced his upper lip where the salt-sweet, sticky residue of Derek’s milk lingered. He looked down, his gaze met Derek’s. Lips stretched wide around his fat cock, the dairy-were gave a soft whine. His wide green eyes, red-rimmed from crying seemed to silently beseech him. What ever happened at Argent’s it was clear the milker was more than desperate to stay with his new owner.

“I’m sure we can work something out…” Deaton panted, his climax rushing towards him. “After all... I-I’ve a-always been invested in my patients b-best interests...”

“We have a deal then?”

It was unorthodox and unprofessional but it would ensure Derek stayed in a good home and was well cared for. Not to mention, within his reach.

Yes!” Deaton shouted, coming and coming to an agreement on Derek’s behalf.

It was an act of kindness he was agreeing to, really.

 

**Author's Note:**

> Yup... My brain is warped. There's not much more I can say...
> 
> Hope you enjoyed this way more than Derek did.
> 
> P.S. I would give my left nut for someone to draw dairy-were Derek.


End file.
